Chemoenzymatic Synthesis of Stegobinone and Stegobiol, Components of the Natural Sex Pheromone of the Drugstore Beetle (Stegobium paniceum L.)



NADPH-dependent ketoreductases were used for the chemoenzymatic stereoselective synthesis of the two componentsof the natural sex pheromone of the drugstore beetle. The key step in the asymmetric synthesis was the enzymatic reduction of an α-methyl-1,3-diketone and an α-methyl-β-keto ester, which finally led to the preparation of crystalline stegobinone and stegobiol.